My Jerkoff History

The first time I jerked off, I was playing with my hard dick one Saturday morning. I was rubbing the top sheet across the back of the head of my dick, enjoying the pleasant sensations. Suddenly, I felt a strange tingling that became stronger, then subsided. My dick was too sensitive to touch. I panicked, thinking I had somehow broken my friend, and inspected it carefully, pulling down the sheet, fully expecting to see blood. Nothing. I was instantly addicted, and repeated the sheet rub every night.

My first time with a boy was a few months later. My friend Tommy from across the street told me about..the pulley..and then proceeded to show me. He pulled down his pants, placed the head of his small dick in his palm, then wrapped his fingers around it down to the base. He then proceeded to pull his hand up and down, until he orgasmed. I quickly related to him about my sheet rub experiences, and repeated the pulley, orgasming for the first time with my hand. There was no guilt in either of us. Neither of us knew what we were doing, and neither had even heard of homosexuality, or sex. My second time with a boy was Ricky later that summer, who lived several blocks away. He was four years older than me, and he asked me one day if I jerked off. It was the first time I had heard the term, and asked him what he meant. He led me to his bedroom, locked the door, dropped his pants and revealed what I thought was a monster. He was a good twice the size of me, had pubic hair, and hairy ballsack. He started jerking off, in the traditional fist method, and I watched. He told me to take my pants off and I did, revealing my small hairless, but very erect dick. He reached over and started to jerk me, the first time anyone had ever touched me. He took my hand placed it on his dick, and I wrapped my hand around that monster, and stroked him. When he orgasmed, I saw my first semen, and was shocked. He laughed, and explained about baby makers, his term for semen, and promised me I would start shooting soon too.

Ricky was gay, something I didn't understand until later. He was also constantly horny, and would use me to get off as much as possible. I still didn't feel guilty about it, because it felt so good. Ricky went from mutual handjobs, to laying on top of me, putting oil on my stomach and dick, then rubbing himself against me until he came. After a few months of that, Ricky asked me to blow him. I got within an inch of doing it, but the aroma of his dick totally turned me off, and I refused. Looking back, Ricky definitely used me. Fortunately, my family moved not long after. By this time, I was beating the meat at least twice a day, and up to six times a day. From the first time I spurted semen, and learned that my days of being able to jerk off again immediately were sadly over, but I was still having multiple orgasms a day.

By the time I was 16, my dick had grown to six inches. I finally got a girl that would go out with me, and we moved through the stages of kissing, me groping her tits, and finally getting my hand into her pants. Without a clue to what I was doing, I sat in the darkness of Beckys basement groping and jabbing a finger into her. I thought my dick was going to explode the first time I felt the wetness of Beckys pussy on my fingertips. Becky pulled my hand off her, and turned on the lamp. I stared at her crotch. What a sight! Her legs were splayed open, her shorts and panties around her thighs. Her round breast pulled out of her still attached bra, its large pink nipple erect and glistening from my saliva. She took my index finger, and gently placed it on her clit. She instructed me to lightly stroke it, which I did. I stared at that tiny little pink nub, her wispy blond hairs not concealing it.

I studied her pussy lips. She became wetter, and gyrated on the sofa, she whispered for me to go faster, and my finger blurred across her pussy, she threw her head back, and sighed, then quickly pulled my hand away. She smiled, thrust her tongue into my mouth, and rubbed my crotch. She pulled my shorts off, and began jerking me off. I stared at her exposed breast and pussy, and shot onto my t-shirt in less than 30 seconds in an incredibly strong orgasm. She grabbed the tissue box, grabbed several for herself, then handed it to me, and I tried to clean up my mess as best I could, as she wiped her pussy of its juices. We smiled at each other like Cheshire cats, and pulled our clothes back on. I was still hard, and tried to get her to go for round two, and she said tomorrow. She told me to go flush the tissues before her parents got home to hide the evidence. I flushed mine, and slipped hers into my pocket. As I walked home, I sniffed my fingers of that wonderful aroma, then jerked off three times sniffing her tissue.

I had several other girlfriends in high school, finally losing my virginity at 17, but remember the fingering and handjobs with each of them. Angela with the large black bush and clit the size of my pinkie. Allison, whose older brother walked in on us while we were buttnaked, humping each others hands.

In high school, I had two guys hint around about messing together, and I turned both of them down. By college, I was jerking off probably 20 times a week. Having a roommate produced a lot of timing issues, but still managed to rub one out in privacy at least twice a day. My roommate John was a great guy, but our masturbation habits were never discussed, even though he had a habit of leaving his spent tissues to accumulate under his bunk bed, and I often returned from my morning shower to that familiar smell of semen.

One night we were out drinking, and picked up an older (maybe 25?) German woman who was drunk, and got her back to our dorm room. In no time, we were all naked on Johns twin bed, and it got kinky. She alternated jacking John and jerking me, and jerking John while I played with her tits. She pulled our dicks together, our heads touching, and wrapped both hands around the two dicks, pressed them together, and jerked us off. It was the first time my dick was touching another dick since Ricky. I had forgotten the heat that emanates from another guys dick, and the use of her saliva made it slippery. She mumbled how she wanted both of them in her at the same time, and that sent John over, and his cum hit both of us. She furiously jerked me with his juice, and I came shortly.

After we dumped her back at the bar, we walked back to the dorm in the early morning. We were laughing, and reliving the event. When we got back to the dorm, we stripped down for bed, discussing Inga. John said he had never touched another guys dick before, and I didnt say anything. He asked me point blank if I had, and I told him about Ricky. Then I confessed that when we were being pumped by Inga, it felt just like when Ricky would hump against me. Without a word, he stood up, came to my bed, and laid on top of me, his hardon pressed against my stomach. He started to grind into me, and I wrapped my arms around his waist and pulled him up and down on top of me. We ground for about 15 minutes before I came, and then a few minutes later, John came.

The next morning it was very awkward. We both had dried cum on our stomachs and on our sheets. We never did it again, and never discussed it. I must admit, I still jerk off thinking about that night.